CA1173033A - Preparation de pyridazines substituees par des bases, et applications - Google Patents

Preparation de pyridazines substituees par des bases, et applications

Info

Publication number: CA1173033A
Authority: CA; Canada
Prior art keywords: atoms; formula; hydrogen; starting substance; employed
Prior art date: 1980-12-22
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000391595A

Other languages

English (en)

Inventor

Thomas Raabe

Helmut Bohn

Piero A. Martorana

Rolf-Eberhard Nitz

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Sanofi Aventis Deutschland GmbH

Original Assignee

Cassella AG

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1980-12-22

Filing date

1981-12-07

Publication date

1984-08-21

1981-12-07 Application filed by Cassella AG filed Critical Cassella AG

1984-08-21 Application granted granted Critical

1984-08-21 Publication of CA1173033A publication Critical patent/CA1173033A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 35
150000004892 pyridazines Chemical class 0.000 title claims abstract description 9
150000001875 compounds Chemical class 0.000 claims abstract description 105
239000002253 acid Substances 0.000 claims abstract description 39
150000003839 salts Chemical class 0.000 claims abstract description 23
229910052736 halogen Inorganic materials 0.000 claims abstract description 8
150000002367 halogens Chemical class 0.000 claims abstract description 8
-1 benzyloxy, phenethoxy Chemical group 0.000 claims description 93
125000004432 carbon atom Chemical group C* 0.000 claims description 85
229910052739 hydrogen Inorganic materials 0.000 claims description 46
239000001257 hydrogen Substances 0.000 claims description 46
239000000126 substance Substances 0.000 claims description 30
239000000460 chlorine Substances 0.000 claims description 23
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
125000000217 alkyl group Chemical group 0.000 claims description 13
125000001424 substituent group Chemical group 0.000 claims description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
229940012017 ethylenediamine Drugs 0.000 claims description 10
150000002431 hydrogen Chemical class 0.000 claims description 10
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
229910052801 chlorine Inorganic materials 0.000 claims description 9
125000003342 alkenyl group Chemical group 0.000 claims description 8
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 8
125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 8
125000000753 cycloalkyl group Chemical group 0.000 claims description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
229910052794 bromium Inorganic materials 0.000 claims description 7
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 6
229910052731 fluorine Inorganic materials 0.000 claims description 6
239000011737 fluorine Substances 0.000 claims description 6
125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
238000010438 heat treatment Methods 0.000 claims description 5
238000007327 hydrogenolysis reaction Methods 0.000 claims description 5
125000003302 alkenyloxy group Chemical group 0.000 claims description 4
125000006193 alkinyl group Chemical group 0.000 claims description 4
125000001589 carboacyl group Chemical group 0.000 claims description 4
125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
VJWXIRQLLGYIDI-UHFFFAOYSA-N 4,5-dichloro-1h-pyridazin-6-one Chemical compound OC1=NN=CC(Cl)=C1Cl VJWXIRQLLGYIDI-UHFFFAOYSA-N 0.000 claims description 3
125000004442 acylamino group Chemical group 0.000 claims description 3
125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
ACKBTCUMGAHRIE-UHFFFAOYSA-N 4,5-dichloro-2-methylpyridazin-3-one Chemical compound CN1N=CC(Cl)=C(Cl)C1=O ACKBTCUMGAHRIE-UHFFFAOYSA-N 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
FQSMVZSHMHKFSN-UHFFFAOYSA-N 4-chloro-5-[2-[[3-(2-ethoxyphenoxy)-2-hydroxypropyl]amino]ethylamino]-2-methylpyridazin-3-one Chemical compound CCOC1=CC=CC=C1OCC(O)CNCCNC1=C(Cl)C(=O)N(C)N=C1 FQSMVZSHMHKFSN-UHFFFAOYSA-N 0.000 claims 3
238000004519 manufacturing process Methods 0.000 claims 3
LLPRPSRBNWKTOC-UHFFFAOYSA-N 1-(2-aminoethylamino)-3-(2-chlorophenoxy)propan-2-ol Chemical compound NCCNCC(O)COC1=CC=CC=C1Cl LLPRPSRBNWKTOC-UHFFFAOYSA-N 0.000 claims 1
PIUBPWUEYGXXNM-UHFFFAOYSA-N 1-(2-aminoethylamino)-3-(2-ethoxyphenoxy)propan-2-ol Chemical compound CCOC1=CC=CC=C1OCC(O)CNCCN PIUBPWUEYGXXNM-UHFFFAOYSA-N 0.000 claims 1
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
SKZJNEFPRPMLHK-UHFFFAOYSA-N 5-[2-(benzylamino)ethylamino]-2-butyl-4-chloropyridazin-3-one Chemical compound O=C1N(CCCC)N=CC(NCCNCC=2C=CC=CC=2)=C1Cl SKZJNEFPRPMLHK-UHFFFAOYSA-N 0.000 claims 1
UUWABVCZFXKHSU-UHFFFAOYSA-N 5-chloro-4-[2-[[3-(2-chlorophenoxy)-2-hydroxypropyl]amino]ethylamino]-1h-pyridazin-6-one Chemical compound C=1C=CC=C(Cl)C=1OCC(O)CNCCNC=1C=NNC(=O)C=1Cl UUWABVCZFXKHSU-UHFFFAOYSA-N 0.000 claims 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
238000006243 chemical reaction Methods 0.000 abstract description 31
235000013350 formula milk Nutrition 0.000 description 65
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
150000003254 radicals Chemical class 0.000 description 21
239000002904 solvent Substances 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
239000000203 mixture Substances 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
238000007792 addition Methods 0.000 description 11
IUBSYMUCCVWXPE-UHFFFAOYSA-N metoprolol Chemical compound COCCC1=CC=C(OCC(O)CNC(C)C)C=C1 IUBSYMUCCVWXPE-UHFFFAOYSA-N 0.000 description 11
229960002237 metoprolol Drugs 0.000 description 11
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
239000002270 dispersing agent Substances 0.000 description 9
239000007858 starting material Substances 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
238000010992 reflux Methods 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000011230 binding agent Substances 0.000 description 6
239000000306 component Substances 0.000 description 6
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
150000001298 alcohols Chemical class 0.000 description 5
230000009249 intrinsic sympathomimetic activity Effects 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
125000006239 protecting group Chemical group 0.000 description 5
239000008096 xylene Substances 0.000 description 5
229940074411 xylene Drugs 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
229950005499 carbon tetrachloride Drugs 0.000 description 4
230000000747 cardiac effect Effects 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
229960001701 chloroform Drugs 0.000 description 4
229960001760 dimethyl sulfoxide Drugs 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
FBBDOOHMGLLEGJ-UHFFFAOYSA-N methane;hydrochloride Chemical compound C.Cl FBBDOOHMGLLEGJ-UHFFFAOYSA-N 0.000 description 4
229940073584 methylene chloride Drugs 0.000 description 4
WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
229940093956 potassium carbonate Drugs 0.000 description 4
239000000376 reactant Substances 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
241000282472 Canis lupus familiaris Species 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
125000005263 alkylenediamine group Chemical group 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
230000000875 corresponding effect Effects 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
230000000004 hemodynamic effect Effects 0.000 description 3
230000001077 hypotensive effect Effects 0.000 description 3
230000036581 peripheral resistance Effects 0.000 description 3
239000000825 pharmaceutical preparation Substances 0.000 description 3
KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
LUMLZKVIXLWTCI-NSCUHMNNSA-N (e)-2,3-dichloro-4-oxobut-2-enoic acid Chemical compound OC(=O)C(\Cl)=C(/Cl)C=O LUMLZKVIXLWTCI-NSCUHMNNSA-N 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
206010002091 Anaesthesia Diseases 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
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OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
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239000000654 additive Substances 0.000 description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
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150000001408 amides Chemical group 0.000 description 2
230000037005 anaesthesia Effects 0.000 description 2
230000003288 anthiarrhythmic effect Effects 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 2
150000008282 halocarbons Chemical class 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
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125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
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WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
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239000002798 polar solvent Substances 0.000 description 2
LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
238000003756 stirring Methods 0.000 description 2
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OXQGTIUCKGYOAA-UHFFFAOYSA-N 2-Ethylbutanoic acid Chemical compound CCC(CC)C(O)=O OXQGTIUCKGYOAA-UHFFFAOYSA-N 0.000 description 1
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125000006040 2-hexenyl group Chemical group 0.000 description 1
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
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239000000174 gluconic acid Substances 0.000 description 1
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210000003205 muscle Anatomy 0.000 description 1
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ACYBVNYNIZTUIL-UHFFFAOYSA-N n'-benzylethane-1,2-diamine Chemical compound NCCNCC1=CC=CC=C1 ACYBVNYNIZTUIL-UHFFFAOYSA-N 0.000 description 1
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238000010647 peptide synthesis reaction Methods 0.000 description 1
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MRBDMNSDAVCSSF-UHFFFAOYSA-N phentolamine Chemical compound C1=CC(C)=CC=C1N(C=1C=C(O)C=CC=1)CC1=NCCN1 MRBDMNSDAVCSSF-UHFFFAOYSA-N 0.000 description 1
229960001999 phentolamine Drugs 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
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235000007686 potassium Nutrition 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000036316 preload Effects 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
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238000011321 prophylaxis Methods 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
229940095574 propionic acid Drugs 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
229960001404 quinidine Drugs 0.000 description 1
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230000036647 reaction Effects 0.000 description 1
238000012552 review Methods 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
239000011833 salt mixture Substances 0.000 description 1
229940125723 sedative agent Drugs 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000000243 solution Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
229940127230 sympathomimetic drug Drugs 0.000 description 1
230000001975 sympathomimetic effect Effects 0.000 description 1
230000035488 systolic blood pressure Effects 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
229960001367 tartaric acid Drugs 0.000 description 1
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230000001225 therapeutic effect Effects 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229940124549 vasodilator Drugs 0.000 description 1
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235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
230000002861 ventricular Effects 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/22—Nitrogen and oxygen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Cardiology (AREA)
General Health & Medical Sciences (AREA)
Hospice & Palliative Care (AREA)
Heart & Thoracic Surgery (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pyridine Compounds (AREA)
Solid-Sorbent Or Filter-Aiding Compositions (AREA)

CA000391595A 1980-12-22 1981-12-07 Preparation de pyridazines substituees par des bases, et applications Expired CA1173033A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19803048487 DE3048487A1 (de)	1980-12-22	1980-12-22	Basisch substituierte pyridazine, ihre herstellung und ihre verwendung
DEP3048487.8		1980-12-22

Publications (1)

Publication Number	Publication Date
CA1173033A true CA1173033A (fr)	1984-08-21

Family

ID=6119960

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000391595A Expired CA1173033A (fr)	1980-12-22	1981-12-07	Preparation de pyridazines substituees par des bases, et applications

Country Status (26)

Country	Link
US (1)	US4532239A (fr)
EP (1)	EP0054946B1 (fr)
JP (1)	JPS57128677A (fr)
KR (1)	KR880002233B1 (fr)
AT (1)	ATE8991T1 (fr)
AU (1)	AU544386B2 (fr)
CA (1)	CA1173033A (fr)
CS (1)	CS236665B2 (fr)
DD (1)	DD202013A5 (fr)
DE (2)	DE3048487A1 (fr)
DK (1)	DK149810C (fr)
ES (3)	ES8304941A1 (fr)
FI (1)	FI73418C (fr)
GR (1)	GR81382B (fr)
HK (1)	HK51485A (fr)
IE (1)	IE51985B1 (fr)
IL (1)	IL64605A (fr)
NO (1)	NO814182L (fr)
NZ (1)	NZ198919A (fr)
PH (1)	PH17529A (fr)
PL (3)	PL137150B1 (fr)
PT (1)	PT74185B (fr)
RO (3)	RO84277B (fr)
SG (1)	SG7585G (fr)
SU (2)	SU1170970A3 (fr)
ZA (1)	ZA818806B (fr)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3023369A1 (de) *	1980-06-23	1982-01-14	Boehringer Mannheim Gmbh, 6800 Mannheim	Aryloxypropanolamine, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
JPH0641454B2 (ja) *	1985-02-27	1994-06-01	日産化学工業株式会社	ピリダジノン誘導体
US4892947A (en) *	1985-04-27	1990-01-09	Nissan Chemical Industries Ltd.	3(2H)Pyridazinone, process for its preparation and anti-allergic agent containing it
JPS61282194A (ja) *	1985-06-06	1986-12-12	Yukio Nakamura	ジエツト推進式舟艇の推進軸とその製造法
JPH0629254B2 (ja) *	1986-09-08	1994-04-20	帝国臓器製薬株式会社	ピリダジノン誘導体
DE3902316A1 (de) *	1989-01-26	1990-08-02	Lentia Gmbh	Neue piperazinylalkyl-3(2h)-pyridazinone, verfahren zu ihrer herstellung und ihre verwendung als blutdrucksenkende mittel
NZ234087A (en) *	1989-06-19	1991-08-27	Teikoku Hormone Mfg Co Ltd	2-(3-aryloxy(2-hydroxy-propylamino))-2-methylpropyl- aminophenyl pyridazine derivatives
US5221674A (en) *	1989-06-19	1993-06-22	Teikoku Hormone Mfg. Co., Ltd.	Pyridazinone derivatives
HU214320B (hu) *	1991-12-20	1998-03-02	EGIS Gyógyszergyár Rt.	Eljárás új 3(2H)-piridazinon-származékok és ezeket tartalmazó gyógyszerkészítmények előállítására
AU752967B2 (en) *	1998-06-05	2002-10-03	Egis Gyogyszergyar Rt.	Process for the preparation of a 3(2H)-pyridazinone- 4-substituted amino- 5-chloro- derivative
KR20100049500A (ko) *	2007-03-15	2010-05-12	쉐링 코포레이션	글루칸 신타제 억제제로서 유용한 피리다지논 유도체

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BE741762A (fr) *	1968-11-18	1970-05-19
GB1421999A (en) *	1973-02-08	1976-01-21	Smith Kline French Lab	Heterocyclic containing sulphoxides
US4115575A (en) *	1973-02-20	1978-09-19	Ciba-Geigy Corporation	2-(3-Amino-2-hydroxy-propoxy)-pyrazines
GB1488330A (en) *	1973-12-19	1977-10-12	Smith Kline French Lab	Dihydropyridazinones
US4088764A (en) *	1973-12-27	1978-05-09	Cassella Farbwerke Mainkur Aktiengesellschaft	Pharmaceutically active derivatives of 1-phenoxy-3-amino-propan-2-ol
CH592625A5 (fr) *	1974-05-14	1977-10-31	Ciba Geigy Ag
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DD146749A3 (de) *	1977-12-01	1981-03-04	Dieter Lehmann	Verfahren zur herstellung von phenoxyalkanolamin-derivaten
DE3023369A1 (de) *	1980-06-23	1982-01-14	Boehringer Mannheim Gmbh, 6800 Mannheim	Aryloxypropanolamine, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel

1980
- 1980-12-22 DE DE19803048487 patent/DE3048487A1/de not_active Withdrawn
1981
- 1981-11-10 NZ NZ198919A patent/NZ198919A/xx unknown
- 1981-12-07 CA CA000391595A patent/CA1173033A/fr not_active Expired
- 1981-12-08 DK DK542881A patent/DK149810C/da not_active IP Right Cessation
- 1981-12-08 NO NO814182A patent/NO814182L/no unknown
- 1981-12-08 FI FI813941A patent/FI73418C/fi not_active IP Right Cessation
- 1981-12-17 CS CS819455A patent/CS236665B2/cs unknown
- 1981-12-17 DD DD81235901A patent/DD202013A5/de unknown
- 1981-12-18 PL PL1981238537A patent/PL137150B1/pl unknown
- 1981-12-18 PL PL1981234312A patent/PL136127B1/pl unknown
- 1981-12-18 PL PL1981238538A patent/PL137106B1/pl unknown
- 1981-12-19 AT AT81110620T patent/ATE8991T1/de not_active IP Right Cessation
- 1981-12-19 DE DE8181110620T patent/DE3165595D1/de not_active Expired
- 1981-12-19 EP EP81110620A patent/EP0054946B1/fr not_active Expired
- 1981-12-21 GR GR66860A patent/GR81382B/el unknown
- 1981-12-21 KR KR1019810005043A patent/KR880002233B1/ko not_active Expired
- 1981-12-21 RO RO106060A patent/RO84277B/ro unknown
- 1981-12-21 PH PH26659A patent/PH17529A/en unknown
- 1981-12-21 RO RO113112A patent/RO88201B/ro unknown
- 1981-12-21 RO RO113111A patent/RO88190B/ro unknown
- 1981-12-21 ZA ZA818806A patent/ZA818806B/xx unknown
- 1981-12-21 JP JP56205363A patent/JPS57128677A/ja active Pending
- 1981-12-21 SU SU813367148A patent/SU1170970A3/ru active
- 1981-12-21 IL IL64605A patent/IL64605A/xx unknown
- 1981-12-21 IE IE3014/81A patent/IE51985B1/en unknown
- 1981-12-21 AU AU78704/81A patent/AU544386B2/en not_active Ceased
- 1981-12-22 ES ES508274A patent/ES8304941A1/es not_active Expired
- 1981-12-22 PT PT74185A patent/PT74185B/pt unknown
1982
- 1982-08-20 SU SU823478901A patent/SU1151204A3/ru active
- 1982-12-13 ES ES518139A patent/ES518139A0/es active Granted
- 1982-12-13 ES ES518138A patent/ES8400096A1/es not_active Expired
1983
- 1983-12-20 US US06/563,538 patent/US4532239A/en not_active Expired - Fee Related
1985
- 1985-01-26 SG SG75/85A patent/SG7585G/en unknown
- 1985-07-04 HK HK514/85A patent/HK51485A/xx unknown

Also Published As

Publication number	Publication date
ES8308859A1 (es)	1983-10-01
KR880002233B1 (ko)	1988-10-20
KR830007577A (ko)	1983-11-04
DD202013A5 (de)	1983-08-24
RO88190A (fr)	1985-12-30
IE51985B1 (en)	1987-05-13
DE3165595D1 (en)	1984-09-20
GR81382B (fr)	1984-12-11
PL238537A1 (en)	1983-06-20
FI813941L (fi)	1982-06-23
RO88201A (fr)	1985-12-30
PL238538A1 (en)	1983-04-25
EP0054946B1 (fr)	1984-08-15
FI73418C (fi)	1987-10-09
NZ198919A (en)	1985-05-31
ES518138A0 (es)	1983-10-16
SU1170970A3 (ru)	1985-07-30
IE813014L (en)	1982-06-22
SG7585G (en)	1985-08-08
ES8400096A1 (es)	1983-10-16
PL136127B1 (en)	1986-01-31
FI73418B (fi)	1987-06-30
DK149810B (da)	1986-10-06
SU1151204A3 (ru)	1985-04-15
DE3048487A1 (de)	1982-07-29
JPS57128677A (en)	1982-08-10
PL137106B1 (en)	1986-04-30
AU544386B2 (en)	1985-05-23
RO88190B (ro)	1985-12-31
PT74185A (de)	1982-01-01
ZA818806B (en)	1982-11-24
RO88201B (ro)	1985-12-31
HK51485A (en)	1985-07-12
ES508274A0 (es)	1983-03-16
ES518139A0 (es)	1983-10-01
PL137150B1 (en)	1986-05-31
PT74185B (de)	1987-03-24
PH17529A (en)	1984-09-13
IL64605A0 (en)	1982-03-31
RO84277A (fr)	1984-05-23
RO84277B (ro)	1984-07-30
NO814182L (no)	1982-06-23
ATE8991T1 (de)	1984-09-15
DK542881A (da)	1982-06-23
PL234312A1 (en)	1983-02-14
EP0054946A1 (fr)	1982-06-30
CS236665B2 (en)	1985-05-15
US4532239A (en)	1985-07-30
DK149810C (da)	1987-03-23
ES8304941A1 (es)	1983-03-16
IL64605A (en)	1985-11-29
AU7870481A (en)	1982-07-01

Legal Events

Date	Code	Title	Description
2001-08-22	MKEC	Expiry (correction)
2001-12-07	MKEX	Expiry

Publication	Publication Date	Title
CA1173033A (fr)	1984-08-21	Preparation de pyridazines substituees par des bases, et applications
DK159442B (da)	1990-10-15	Analogifremgangsmaade til fremstilling af 6,7-substitueret-4-ethyl-quinazoliner
US4978665A (en)	1990-12-18	3(2H)pyridazinone, and antagonistic agent against SRS-A containing it
EP0186817B1 (fr)	1989-08-02	(2H)-Pyridazinone-3, procédé pour sa préparation et agent antiallergique la contenant
US3944551A (en)	1976-03-16	N-Coumaranyl and chromanyl -methyl-or sulfur analogs thereof-N'- thiazolyl piperazines
CA1085842A (fr)	1980-09-16	Procedes d'obtention de derives d'alkylenediamine
US3957786A (en)	1976-05-18	Aryl-substituted piperazinyl-alkylamino-uracils, -uracil ethers and -uracil thioethers and method for their production
SE437517B (sv)	1985-03-04	3-(1-pyrazolyl)-pyridazinderivat
CA1217490A (fr)	1987-02-03	Composes heterocycliques agissant sur le snc, procede de preparation et composes pharmaceutiques les contenant
CA1094560A (fr)	1981-01-27	Derives de la piperazine
EP0201765B1 (fr)	1991-09-18	3 (2H) Pyridazinones, procédé de préparation et agents antiallergiques les contenant
US4353904A (en)	1982-10-12	Phenylpiperazine derivatives of 1,3,4-oxadiazolylphenols, and therapeutic agents containing these compounds
CA1131641A (fr)	1982-09-14	Derives de piperazinyl-tetrahydronaphtalene
GB1578971A (en)	1980-11-12	8-hydroxy-5-(3-amino-2-hydroxypropoxy) carbostyrils and derivatives thereof
JP4472337B2 (ja)	2010-06-02	アルキルアミノピリダジノン誘導体、この調製方法、およびこれを含む医薬組成物
CA1181070A (fr)	1985-01-15	Methode de preparation de derives de l'acide 2- hydroxyoxanilique
US4716161A (en)	1987-12-29	Phenylpiperazine derivatives and their acid addition salts
US4399137A (en)	1983-08-16	6-Imidazol-1-yl-3-hydrazino-pyridazines, their preparation and antihypertensive use
US4438143A (en)	1984-03-20	1-Aryloxy-3-alkylamino-2-propanols and pharmaceutical compositions containing them
US3978057A (en)	1976-08-31	Substituted amino-hydrazinopyridazines
US4267187A (en)	1981-05-12	Aminopropanol derivatives of 2-(0-hydroxyphenyl)-pyrrole
US4820821A (en)	1989-04-11	Novel pyridazinone-imines and their physiologically tolerated addition salts with acids, their preparation and therapeutic agents containing these compounds
SI9300609A (en)	1994-06-30	New heterocyclic compounds with antiastmatic/antialergic, antiinflammatory, positively ionotropic and anti-hypertensive activity
EP0066144B1 (fr)	1986-02-19	Dérivés de benzylazole
CA1165324A (fr)	1984-04-10	1-aryloxy-3-alkylamino-propan-2-ols, et methodes pour les preparer